Petasin

Petasin

Names
IUPAC name (1R,2R,7S,8aR)-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate
Other names Petasol butenoate; O-Angeloylsencathenone
Identifiers
CAS Number	26577-85-5
ChEBI	CHEBI:8030
ChemSpider	4444859
Jmol interactive 3D	Image
PubChem	5281526
InChI InChI=1S/C20H28O3/c1-7-13(4)19(22)23-18-9-8-15-10-17(21)16(12(2)3)11-20(15,6)14(18)5/h7,10,14,16,18H,2,8-9,11H2,1,3-6H3/b13-7-/t14-,16-,18+,20+/m0/s1 Key: ISTBXSFGFOYLTM-NZEDGPFZSA-N InChI=1/C20H28O3/c1-7-13(4)19(22)23-18-9-8-15-10-17(21)16(12(2)3)11-20(15,6)14(18)5/h7,10,14,16,18H,2,8-9,11H2,1,3-6H3/b13-7-/t14-,16-,18+,20+/m0/s1 Key: ISTBXSFGFOYLTM-NZEDGPFZBZ
SMILES O=C2/C=C1/CC[C@@H](OC(=O)\C(=C/C)C)[C@@H]([C@]1(C[C@H]2\C(=C)C)C)C
Properties
Chemical formula	C20H28O3
Molar mass	316.44 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Petasin is a natural chemical compound found in plants of the genus Petasites. Chemically, it is classified as a sesquiterpene and is the ester of petasol and angelic acid.

Petasin is believed to be responsible, at least in part, for the anti-inflammatory effects of Common Butterbur (Petasites hybridus) extracts.^[1]

References

1. Thomet, O; Wiesmann, UN; Schapowal, A; Bizer, C; Simon, HU (2001). "Role of petasin in the potential anti-inflammatory activity of a plant extract of petasites hybridus". Biochemical Pharmacology 61 (8): 1041–7. doi:10.1016/S0006-2952(01)00552-4. PMID 11286996.